Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Grunwaldzka 6, 60-780 Poznan, Poland.
Department of Genetics and Pharmaceutical Microbiology, Poznan University of Medical Sciences, Swiecickiego 4, 60-781 Poznan, Poland.
J Photochem Photobiol B. 2018 Nov;188:100-106. doi: 10.1016/j.jphotobiol.2018.09.003. Epub 2018 Sep 12.
Photophysical properties and photodynamic antibacterial potential of magnesium phthalocyanines bearing 2-propoxy, benzyloxy, 3,5-bis(benzyloxy)benzyloxy substituents at non-peripheral positions were studied. The UV-Vis absorption spectra of researched phthalocyanine derivatives were found typical. Extension of peripheral substituent size from 2-propoxy to benzyloxy and finally 3,5-bis(benzyloxy)benzyloxy was accompanied by the rise of quantum yield of fluorescence up to 0.17 and 0.04 in DMF and DMSO, respectively. Similarly, the expansion of the phthalocyanine periphery from the 2-propoxy to benzyloxy and 3,5-bis(benzyloxy)benzyloxy groups resulted in a detectable increase of the singlet oxygen quantum yield values to 0.04, 0.12, 0.14 respectively, which was assessed following direct method of singlet oxygen phosphorescence measurement at 1270 nm. Studied phthalocyanines undergo photobleaching process with the quantum yields at the level of 10 in DMSO and 10 in DMF. The size of phthalocyanine impacted the process of liposomal formulation. Small liposome vesicles containing non-peripherally substituted phthalocyanines with 2-propoxy and benzyloxy substituents were obtained following extrusion method. The unification process of the liposomes loaded with 3,5-bis(benzyloxy)benzyloxy non-peripherally substituted phthalocyanines was not possible. In in vitro antimicrobial photodynamic inactivation study, log reduction values of bacterial (Enterococcus faecalis) growth at 3.61 and 2.99 were achieved for liposomal formulations containing phthalocyanines with 2-propoxy and benzyloxy substituents respectively, whereas phthalocyanine with 3,5-bis(benzyloxy)benzyloxy substituents was inactive. Phthalocyanine with 2-propoxy substituents exhibited relatively low toxicity in Vibrio fischeri bioluminescence test, whereas phthalocyanine with benzyloxy substituents revealed intense bioluminescence, which could be associated with hormesis phenomenon.
研究了具有 2-丙氧基、苄氧基和 3,5-双（苄氧基）苄氧基等非外围取代基的镁酞菁的光物理性质和光动力抗菌潜力。研究发现，所研究的酞菁衍生物的紫外-可见吸收光谱具有典型特征。将外围取代基的尺寸从 2-丙氧基扩展到苄氧基，最后扩展到 3,5-双（苄氧基）苄氧基，导致荧光量子产率分别提高到 0.17 和 0.04（在 DMF 和 DMSO 中）。同样，将酞菁的外围从 2-丙氧基扩展到苄氧基和 3,5-双（苄氧基）苄氧基，导致单线态氧量子产率值分别提高到 0.04、0.12 和 0.14，这是通过直接测量 1270nm 处的单线态氧磷光来评估的。研究的酞菁在 DMSO 中具有 10 级和在 DMF 中具有 10 级的光致漂白量子产率。酞菁的大小影响脂质体制剂的形成过程。通过挤出法获得了含有 2-丙氧基和苄氧基取代基的非外围取代酞菁的小脂质体囊泡。而含有 3,5-双（苄氧基）苄氧基非外围取代基的酞菁则无法进行脂质体的统一过程。在体外抗菌光动力失活研究中，分别含有 2-丙氧基和苄氧基取代基的酞菁的脂质体制剂对细菌（粪肠球菌）生长的对数减少值为 3.61 和 2.99，而含有 3,5-双（苄氧基）苄氧基取代基的酞菁则没有活性。具有 2-丙氧基取代基的酞菁在发光弧菌生物发光试验中表现出相对较低的毒性，而具有苄氧基取代基的酞菁则显示出强烈的生物发光，这可能与赫姆氏现象有关。
